1,3-disubstituted-2-trichloromethyl-5-imino-4-imidazolidinones

ABSTRACT

WHEREIN Y IS OXYGEN OR SULFUR, R1 IS ALKYL OF 1 TO 8 CARBON ATOMS SUBSTITUTED WITH 0 TO 3 HALOGEN ATOMS OR ARYL OF 6 TO 10 CARBON ATOMS SUBSTITUTED WITH 0 TO 3 HALOGEN ATOMS, R2 IS HYDROGEN, R1, AN ALKOXY OF 1 TO 8 CARBON ATOMS OR PHENOXYMETHYL SUBSTITUTED WITH 0 TO 3 HALOGEN ATOMS IN THE BENZENE NUCLEUS. THE COMPOUNDS ARE PESTICIDES AND/OR HERBICIDES.   1-R1,2-(CL3-C-),3-(R2-CO-),4-(NH=),5-(Y=)IMIDAZOLIDINE   COMPOUND OF THE FORMULA

United States Patent 3,721,679 1,3-DISUBS'I'ITUTED-2-TRICHLOROME'IHYL-S-IMINO-4-IMIDAZOLIDINONES Malcolm Scott Singer, Richmond, Calif.,assignor to Chevron Research Company, San Francisco, Calif. No Drawing.Filed Sept. 3, 1970, Ser. No. 69,466 Int. Cl. C07d 49/30 U.S. Cl.260309.7 6 Claims ABSTRACT OF THE DISCLOSURE Compound of the formulawherein Y is oxygen or sulfur, R is alkyl of l to 8 carbon atomssubstituted with 0 to 3 halogen atoms or aryl of 6 to 10 carbon atomssubstituted with 0 to 3 halogen atoms, R is hydrogen, R an alkoxy of lto 8 carbon atoms or phenoxymethyl substituted with 0 to 3 halogen atomsin the benzene nucleus. The compounds are pesticides and/ or herbicides.

BACKGROUND OF THE INVENTION Field The subject invention is directed to1,3-disubstituted- 2-tn'chloromethyl 5 imino-4-imidazolidinones andtheir 4-thi0ne analogs, which find use as herbicides, pesticides, e.g.,fungicides and nematocides.

DESCRIPTION OF THE INVENTION C Ola wherein Y is oxygen or sulfur, R isalkyl of 1 to 8 carbon atoms substituted with 0 to 3 halogen atoms ofatomic number 9 to 35 (fluorine, chlorine or bromine), aryl of 6 tocarbon atoms substituted with 0 to 3 halogen atoms of atomic number 9 to35, R is hydrogen, R (i.e., alkyl of l to 8 carbon atoms substitutedwith 0 to 3 halogen atoms of atomic number 9 to 35 or aryl of 6 to 10carbon atoms substituted with 0 to 3 halogen atoms of atomic number 9 to35), an alkoxy of l to 8 carbon atoms, or phenoxyalkyl the alkyl grouphaving 1 to 4 carbon atoms, substituted with 0 to 3 halogen atoms on thebenzene nucleus.

Preferably R is alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbonatoms substituted with 1 to 3 halogen atoms of atomic number 9 to 35,phenyl, phenyl substituted with 1 to 3 halogen atoms of atomic number 9to 35, R is hydrogen, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4carbon atoms substituted with l to 3 halogen atoms of atomic number 9 to35, phenyl, phenyl substituted with l to 3 halogen atoms of atomicnumber 9 to 35, alkoxy of 1 to 4, carbon atoms, phenoxymethyl orphenoxymethyl substituted with 1 to 3 halogen atoms of atomic number 9to 35 on the benzene nucleus.

Still more preferably Y is oxygen or sulfur, R is alkyl of l to 4 carbonatoms or phenyl, R is hydrogen, alkyl of l to 4 carbon atoms, alkyl of 1to 4 carbon atoms substituted with 1 to 3 halogen atoms of atomic number17 to 35, phenyl, phenyl substituted with 1 to 3 halogen 3,721,679Patented Mar. 20, 1973 atoms of atomic number 17 to 35 or phenoxymethylsubstituted with 1 to 2 halogen atoms of atomic number 17 to 35 on thebenzene nucleus.

. Preferably the halogen substituents for R and R will be chlorine orbromine, or still more preferably chlorine. Preferably the number ofhalogen substituents will not exceed 2 on any particular radical.

Representative radicals which R can represent include methyl, ethyl,n-propyl, isopropyl, n-butyl, isobutyl, pentyl, hexyl, heptyl, octyl,chloromethyl, bromomethyl, fluoromethyl, trichloromethyl, l-chloroethyl,1,1,2-trichloroethyl, 3,3,-trichl0ropropyl, phenyl o-methylphenyl,o-butylphenyl, p-butylphenyl, o-chlorophenyl, p;chlorophenyl,m-bromophenyl, o-chloro-p-bromophenyl.

Representative radicals which R can represent include in addition tothose listed for R hydrogen, phenoxymethyl, phenoxyethyl, phenoxypropyl,phenoxybutyl, ochlorophenoxymethyl, p-chlorophenoxymethyl, 0,p-dichl0-rophenoxymethyl, m-bromophenoxyethyl, methoxy, ethoxy, isopropoxy,butoxy, hexoxy, octoxy, etc.

Representative compounds of the present invention include1-formyl-2-trichloromethyl-3-phenyl-5-imino- 4-imidazolidinone,1-formyl-2-trichloromethyl-3-phenyl-5-imino- 4-imidazolidinethione,1-formyl-2-trichloromethyl-3-methyl-5-imino- 4-imidazolidinone,1-formyl-Z-trichloromethyl-3-o-chlorophenyl- 5-imino-4-imidazolidinone,l-acetyl-.2-trichloromethyl-3-methyl-5-imino- 4-imidazolidinone,l-acetyl-2-trichloromethyl-3-n-butyl-5-imino- 4-imidazolidinone,1-acetyl-2-trichloromethyl-3-phenyl-5-imino- 4-imidazolidinone,1-acetyl-2-triehloromethyl-3-p-butylphenyl-5-imino-4-imidazolidinethione, 1-propionyl-2-trichloromethyl-3-phenyl-S-imino-4-imidazolidinone, 1-butyryl-2-trichloromethyl-3-phenyl-5-imino-4-imidazolidinone, 1-pentanoyl-2-trichloromethyl-3-o,p-dichlorophenyl-S-imino-4-imidazolidinethione,1-hexanoyl-2-trichloromethyl-3-phenyl-5-imino- 4-imidazolidinone,1-octanoyl-2-trich1oromethyl-3-tolyl-5-imino- 4-imidazolidinethione,1-(2-chloroacetyl)-2-trichloromethyl-3-hexyl-5-imino- 4-imidazolidinone,l-(2-bromoacetyl)-2-trichloromethyl 3-phenyl-5-imino- 4-imidazolidinone,l-(3-chloropropionyl)-2-trichloromethyl-3-p-fiuorophenyl-5-imino-4-imidazolidinethione,1-benzoyl-2-trichloromethyl-3-phenyl-5-imino- 4-imidazolidinone,1-benzoyl-2-trichloromethyl-3-n-butyl-5-imino- 4-imidazolidinone,1-benzoyl-2-trichloromethyl-3-phenyl-5-imino- 4-imidazolidinethione,1-(o-chlorobenzoyl)-2-trichloromethyl-3-ethyl-5-imino-4-imidazolidinone, l-phenoxyacetyl-2-trichloromethyl-3-methyl-S-imino-4-imidazolidinone, 1-phenoxypropenyl-2-trichloromethyl-3-ethyl-5-imino-4-imidazolidinethione, 1(2-chlorophenoxyacetyl)-2-trichloromethyl-3-methyl-5-imino-4-imidazolidinone, 1- 3-chlorophenoxyacetyl)-2-trichloromethyl-3-phenyl- 5-imino-4-imidazolidinone,

1 2,4-dichlorophenoxyacetyl -2-trichloromethyl-3-methyl-S-imino-4-imidazolidinethione,

1- 2,4,6-trichlorophenoxybutyryl -2-trichloromethyl-3-methyl-5-imino-4-imidazolidinone,

1- 3-bromophenoxyacetyl -2-trichloromethyl-3-(4-chlorophenyl)-5-imino-4-imidazolidinethione.

The compounds of the present invention-can be prepared by the reactionof an N-substituted cyanoformamide or cyanothioformamide with an N(1,2,2,2 tetrachloroethyl)carboxamide. This reaction may be written asfollows:

wherein R R and Y have the same meaning as before.

In this reaction, approximately equal molar quantities of the reactantsare combined, preferably in an inert solvent. Suitable solvents are thearomatic hydrocarbons such as benzene, toluene, and xylene. The quantityof solvent used is optional, but usually an amount of from about equalweight to about times the weight of the reactants is sufficient. Thereaction is initiated by adding an organic amine base, e.g.,triethylamine, piperidine, trimethylamine, quinuclidine, pyridine, etc.T riethylamine is preferred. At least a molar amount of amine, based onthe carboxamide, is used.

The reaction is carried out at temperatures in the range of 10 C. to 50C., preferably at C. to C. The reaction is exothermic and cooling issometimes used to limit the temperature rise. Typically, batch reactionsare completed in from 1 to 10 hours at ambient temperatures. The productis usually recovered by evaporation of the solvent, followed by a waterWash to remove any amine hydrochloride salt. Purification is readilyaccomplished by recrystallization from a suitable liquid, such asethanol, dimethylformamide/ethanol, isopropanol/water, and1,2-dimethoxyethane.

The N-substituted cyanoformamide and thioformamides used in the abovereaction are readily prepared by the addition of hydrogen cyanide to thecorresponding isocyanate or by treating isothiocyanate with an alkalimetal cyanide, e.g., KCN, in aqueous ethanol followed by acidification.The reactions are as follows:

R N CN MOI wherein R has the same meaning as before and M refers to analkali metal.

Generally a slight molar excess of liquid hydrogen cyanide is added tothe isocyanate dissolved in an inert solvent such as1,2-dimethoxyethane. The quantity of solvent is not critical and mayrange from /2 to 10 times by weight of the isocyanate compound. Thereaction is usually carried out in the cold; that is, temperatures below20 C. For best results, the hydrogen cyanide is added slowly in order tocontrol the temperature. The product may be isolated by evaporating offthe solvent, or preferably it may be used in the solvent without furtherworkup.

For the reaction of the alkali metal cyanide with the isothiocyanate,KCN, is preferred. The alkali metal cyanide should be in slight molarexcess. The solvent should be aqueous ethanol, the quantities not beingcritical and may range from /2 to 10 times by weight of theisothiocyanate compound. The reaction conditions are generally the sameas those indicated above for hydrogen cyanide reacted with isocyanate.Following formation of the intermediate HCl or another acid is added toform the N-substituted thioformamide. Generally the acid will be presentin an equivalent amount to that of the alkali metal cyanide.

The N-(l,2,2,2 tetrachloroethyl)carboxamides are prepared by condensinga carboxamide with chloral, followed by reaction with thionylchloride.This reaction occurs as follows:

wherein R is as defined previously.

The condensation reaction is carried out neat or in a solvent such as anaromatic hydrocarbon, e.g., benzene, toluene, and xylene, or ahalogenated hydrocarbon, e.g., chloroform. The quantity of solvent willusually range from about /2 to 10 times by weight of the carboxamide.Essentially equal molar amounts of chloral and carboxamide are combined,preferably without a solvent at about ambient temperatures, i.e., 1030C. When this reaction is complete, then at least a molar amount ofthionylchloride is added. This reaction is usually carried out atelevated temperatures. Under these conditions, the sulfur dioxide andhydrogen chloride by-products are volatilized from the reaction mixtureas soon as they are formed. The product, when prepared without solvent,may be used as obtained for further reaction. When prepared in a solventit may preferably be used in that solvent Without isolation, or it maybe isolated by evaporation.

The present invention Will be better understood by reference to thefollowing examples of the preparation of representative compounds.

EXAMPLE 1 1-formyl-2-trichloromethyl-3-phenyl-5- imino-4-imidazolidinoneN-phenylcyanoformamide, 7.3 g. (0.05 mole), and N (1,2,2,2tetrachloroethyl)formamide, 10.55 g. (0.05 mole), were mixed with 25 g.of benzene in a ml. flask. Then 5.05 g. (0.05 mole) of triethylamine wasadded slowly with stirring. The temperature rose somewhat. Stirring wascontinued for 4 hours, and then the reaction mixture was allowed tostand for 16 hours. A precipitate was removed by filtration and washedwith water to give 4.7 g. of product having a melting point of 3 C.Analysis for chlorine gave 36.55% (found) vs. 33.25% (calculated). Aninfrared spectra was consistent with the assigned structure and hadstrong adsorption at 690, 830, 1050, 1220, 1475 and 1675 cmf EXAMPLE 21-benzoyl-2-trichloromethyl-3-methyl-S-imino- 4-imidazolidimethioneN-methyl cyanothioformamide, 5.0 g. (0.05 mole), and N-(1,2,2,2tetrachloroethyl)benzamide, 14.3 g. (0.05 mole), were mixed with 25 g.of benzene in a 75 ml. flask. Then 5.0 g. (0.05 mole) of triethylaminewas added slowly. The reaction mixture was allowed to stand 16 hours. Awater soluble precipitate was removed by filtration, and the resultingfiltrate was evaporated to dryness. The solid recovered in this way wasrecrystallized from an ethanol/water solution to give 6.0 g. of product,M.P. 122124 C. Analysis gave chlorine, 29.85%, and sulfur, 9.17%(found), vs. chlorine, 30.42%, and sulfur, 9.13% (calculated). Aninfrared spectra had strong adsorption at 695, 715, 810, 835, 920, 1075,1450 and 1675 cmf Other compounds of the present invention were preparedand are tabulated in Table I.

TABLE I S C1 Melting p oint Compound Calculated Found Calculated Foundl-benzoyl-2-trichloromethy1-3-methy1-5-imino-4-imidazolidinone 31. 9 31.1 136-1401-benzoyl-2-trichloromethyl-3-n-butyl-4-imino-4-irnidazolidinone. 28. 330. 3 110-118 1-(2-chloracetyl) -2-triehloromethyl-tK-phenyl-5-irnino-4-imidazoli dinone 38. 5 36. 6 124-1261-(2-chloroacetyl) -2-trichloromethyl-3-methy1-5-irnino-t-imidazolidione. 46. 3 41. 8 213-215 1-(2-chloroaeetyl)-2-trieh1oromethyl-3-phenyl-5-imino-4-irni dazolidinethione 8. 2 36. 936. 1 130 1-(2-ohloroacetyl) -2-trichlororneth yl-3-me tl1yl-5-imino-4-imi dazolidinethione 10. 0 44. 0 41. 9 1 150 1- (2-chloroacetyl)-2-trichloromethyl-3-n-butyl-fi-iminot-imidazolidinone 40. 7 38. 117-1211-acetyl-2 trichloromethyl-B-methyl-5-imino-4-imidazolidinethione 9 11.1 36. 0 36. 9 114-118 1-(2-ch1orophenoxyacetyl)-2-trichloromethyl-3-5-imin0-4-imidazolidinethion 7. 7 7. 8 34. 2 32. 7176-179 1- (2 ,4-dichlorophenoxyacetyl)-.-trichloromethyl-3-methyl-5-imino-4-irnidazolidinethione 7. 1 7. 2 39.5 37. 5 158-161 1-oarbethoxy-2-triehloromethyl-3-phenyl-5-imino-4-imidazolidinone 2 11. 5 2 10. 4 29. 2 27. 6 75-831-carbethoxy-2-trichloromethyl-tl-phenyl-S-imino--imidazolidinethione 8.41 8. 66 28.0 27. 1 137-140 1 Decomposed. Nitrogen analysis.

UTILITY The compounds of the present invention are useful herbicides andpesticides. In general the compounds are very specific in theiractivity. Thus some of the compounds have activity towards fungi whereasothers have high activity towards viruses, such as tobacco mosaic virus.Others have high activity towards nematodes whereas others have highactivity towards herbicides. Even among those compounds which are usefulas herbicides, there is a great amount of specificity. Thus some of thecompounds are pre-emergence herbicides whereas others are post-emergenceherbicides. Some of the compounds are specific to broadleaved plants asopposed to the grasses.

The compounds of the present invention are herbicidal, with theexception of the compounds in which Y is O and R is alkoxy. Forpre-emergence control of undesirable vegetation these imidazolidinoneswill be applied in herbicidal quantities to the environment, e.g., soilinfested with seeds and/or seedlings of such vegetation. Suchapplication will inhibit the growth of or kill the seeds, germinatingseeds and seedlings. For post-emergence applications theimidazolidinones of the present invention will be applied direct to thefoliage or other plant parts. Some of the compounds are effectiveagainst weed grasses as well as broadleaved weeds. Some are selectivewith respect to the type of application and the type of weed.

The amount of imidazolidinone administered will vary with the particularplant part or plant growth medium which is to be contacted, the generallocation of application, i.e., sheltered areas such as greenhouses ascompared to exposed areas such as fields, as well as the desired type ofcontrol. For pre-emergent control of most plants dosages in the range ofabout 0.5 to lbs. per acre will be used. Such administration will give aconcentration of about 2 to 80 p.p.m. urea distributed throughout 0.1acre-foot. For post-emergence application, such as foliar sprayapplication, compositions containing about 0.5 to 8 lbs. imidazolidinoneper 100 gal. spray will be used. Such application is equivalent to about0.5 to 20 lbs. imidazolidinone per acre.

The herbicidal compositions of this invention comprise a herbicidalamount of one or more of the above described imidazolidinone intimatelyadmixed with a biologically inert carrier. The carrier may be a liquiddiluent in the form of dust powder or granules. These compositions willalso usually contain adjuvants such as a wetting or dispersing agent tofacilitate their penetration into the plant growth media or plant tissueand generally enhance their elfectiveness. These compositions may alsocontain other pesticides, stabilizers, conditioners, fillers and thelike.

Preand post-emergence herbicidal tests on representativeimidazolidinones of this invention were made using the followingmethods:

Pre-emergence test An acetone solution of the test imidazolidinone wasprepared by mixing 750 mg. imidazolidinone, 220 mg. of a nonionicsurfactant and 25 ml. of acetone. This solution was added toapproximately 125 ml. of water containing 156 mg. of surfactant.

Seeds of the test vegetation were planted in a pot of soil and theimidazolidinone solution was sprayed uniformly onto the soil surface ata dose of 100 mg. per cm. The pot was watered and placed in agreenhouse. The pot was watered intermittently and was observed forseedling emergence, health of emerging seedlings, etc. for a 3-weekperiod. At the end of this period the herbicidal effectiveness of theimidazolidinone was rated based on the physiological observations. A Oto 100 scale was used; 0 representing no phytotoxicity, 100 representingcomplete kill.

Post-emergence test The test imidazolidinone was formulated in the samemanner as described above for the pre-emergence test. The concentrationof the imidazolidinone in this formulation was 5000 ppm. Thisformulation was uniformly sprayed on 2 replicate pots of 24-day-oldplants (approximately 15 to 25 plants per pot) at a dose of 100 mg. percm. After the plants had dried, they were placed in a greenhouse andthen watered intermittently at their bases as needed. The plants wereobserved periodically for phytotoxic effects and physiological andmorphological responses to the treatment. After 3 weeks the herbicidaleffectiveness of the imidazolidinone was rated based on theseobservations. A 0 to 100 scale was used; 0 representing nophytotoxicity, 100 representing complete kill.

such as water or acetone or a solid. The solid may be The results ofthese tests appear in Table II.

TABLE II Herbicidal effectiveness, pre/post Compound 0 W C M P L1-formyl-2-trichloromethyl-3-phenyl-5-imino--imidazolidinone 50/- 50/-1-benzoyl-Z-trichloromethy1-3-rnethyl-5-imino-4-im dazol d none -/40 l-benzoy1-2-trichloromethy1-3-n-butyl-5-imino-4-inndazol dinone1-(2-ehloroaeetyl)-2-trichlorornethyl-3-methy1-5-im1no-4;a1rn1dazolldinone0/000 1-(2-chloroacetyl)-2-trichloromethyl-B-phenyl-5-imino-l-1rn1dazoltdrrnethlpne1-(2-c11loroacetyl) -2-trichloromethyl-3-methyl-5-imino4dm1(1&20l1d1m8tl'110n8 50/ 99 /100 /90 --/100l-aeetyl-2-ti'lohlorometh371-3-me%yl-5-irrigiofiimiglazplthneth gne.a...flfinfin23 "0.5876 1- 2-ehloro henox acet l-2-tric orome y- -rne y--1m1no -1m1 21201 no 1 on1-22,4-dichihrophehoxyribetyl)-2-tiiehloromethyl-3-methyl-5-irnino-4-irnidazolidinetluone75/0 85/ 100/ 1026100 12%95 1026100l-carbethoxy-2-triehloromethyl-3-phenyl-5-imino-4-imidazolidin inneNo'rE: O=Wi1d oats (Avena fatua); W=watergrass (Echinochlna crusgalli);C=erabgrass (Digitaria sanguinalis); M=mustard (Brasszca armnsis);P=pigwced (A'maranthus retroflezus); and L=lambsquarter (Ohenopodiumalbum).

The compounds of the present invention find use in the control of fungi.When used as fungicides the imidazolidinones of this invention will beformulated and applied 'in fungicidal amounts by conventional artmethods to fungi or hosts which are subject to fungus attack, especiallyvegetative hosts such as plants, plant seeds, etc. The amount used will,of course, depend upon several factors such as the host, the type offungus, the particular imidazolidinone, etc. The amount generally willrange from 2 to 90%. The imidazolidinones may be combined with inertliquids or solid carriers as powders, solutions, dispersions, etc. forsuch use.

The imidazolidinones of this invention will generally be admixed withbiologically inert liquids or solids in an amount of from about 0.005 to95 weight percent. Higher or lower amounts can be used to advantage.Preferably from 1 to 50 weight percent of the composition will be theimidazolidinones. Typical of the liquid carrier which may be admixedwith the imidazolidinones of this invention include, in addition toacetone, such liquids as water, kerosene, xylene, alcohols, alkylatednaphthylene and glycols. Typical solids which may be incorporated withthe imidazolidinones include the natural clays, such as kaolin clays,diatomaceous earth, synthetic fine silica, talc, pyrophyllite, etc.

Fungicidal formulations may also contain stabilizers, spreading agents,sticking agents, fillers, other compatible pesticides and the like.

To exhibit the activity of certain of the compounds of the presentinvention against fungi, the following test was made.

EXAMPLE A number of the compounds were tested for effectiveness againstspores by means of a variation of The Standard Spore Slide-GerminationMethod for Determining Fungicital Activity, described in the AmericanPhytopathological Society Journal, volume 33, pages 627-632 (1943). Themethod is designed to measure the fungitoxic activity of fungicidalchemicals, their activity being expressed in terms of percent inhibitionof germination of fungus spores. Each compound toxicant to be tested wasdissolved in acetone to a concentration of 100 p.p.m. These solutionswere then pipetted into the wells of depression slides and allowed todry. The wells were filled with a spore suspension of the specified testorganism. A -fold greater volume of suspension was used than that usedto apply the toxicant so that the slide concentration of toxicant was 10p.p.m. The spores were then incubated in a moist chamber overnight. Agroup of 100 spores was examined and the number of spores germinated andnot germinated was counted and recorded to show the biological activityin terms of the percent germination inhibition. Table III reports theresults of this testing.

TABLE IIL-PERCENT CONTROL Some of the compounds of this inventionexhibit good nematocidal activity. In general those compounds wherein Yis O or S, R is alkyl, haloalkyl, aryl or haloaryl, R is alkyl,haloalkyl, aryl or haloaryl are preferred for nematocidal control.Further when R is aryl and R is alkyl, it is preferred that the alkyl beat least ethyl or higher. Thus the imidazolidinones of this inventionmay be used to control plant-parasitic nematodes by exposing them to atoxic amount of the imidazolidinone. Thus, these imidazolidinones willnormally be applied to nematode-infested soil at dosages in the range of3 to 40 lbs. per acre. They may be applied as liquid formulations byspraying or injection. The liquid formulations of these imidazolidinonesmay be solutions, dispersions, or emulsions. Typical solvents which maybe used are aromatics such as xylene, toluene and benzene, ketones suchas cyclohexanone and the like. These liquid formulations will usuallycontain a wetting agent to facilitate the imidazolidinones penetrationinto the soil and generally enhance its effectiveness. They may also beapplied as solid formulations containing carriers such as soil, sawdust,clay and the like. When used as a solid, these imidazolidinones willusually be plowed into the soil. Following their application to thesoil, the soil will be watered to disperse the imidazolidinone belowground level.

The nematocidal activity of several of the imidazolidinones of thisinvention are illustrated by the following method.

A 0.38 ml. portion of a 3% acetone solution of the test compound wasdiluted with 1 ml. acetone. The result ing solution was homogenouslymixed with 20 cc. of vermiculite. The treated vermiculite was then mixedhomogenously with 750 g. of soil, dry weight basis, which was severelyinfested with free-living nematodes (mixed culture of Meloidogynejavanica and Meloidogyne incognita). This mixing gave a concentration ofapproximately 15 parts of the test compound per million parts of soil.This treated soil was stored for 4 days at 65-75 F. It was then dividedequally into 3 parts, each of which was put into a separate pot and keptfor another 3 days. A 3-week old tomato (v. Bonny Best) seedling wasthen transplanted into each pot and incubated for 13 days undergreenhouse conditions. After this period they were removed and the soilwas washed from their roots. The nematocidal effectiveness of the testcompound was determined by observing each plant for signs of nematodeinvasion (number of galls formed, stunting, etc.).

The results of these tests, reported as the average of the 3 replicateson a 0 to 100 basis-0 indicating no effectiveness; 100 indicatingcomplete effectiveness-are reported in Table IV.

TABLE IV.-NEMATOCIDAL ACT IVITY Compound: Percent control l-benzoyl 2trichloromethyl-3-methyl-5-imino- 4-imidazolidinethione 96 l-benzoyl 2trichloromethyl-3-n-butyl-5-imino- 4-imidazolidinone l-(2-chloroacetyl)2 trichloromethyl-3-n-butyl- 5-imino-4-imidazolidinone 81 l-acetyl 2trichloromethyl-3-methyl-5-imino-4- irnidazolidinethione Y=CC=NH whereinY is oxygen or sulfur, R is alkyl of 1 to 8 carbon atoms or phenyl oralkylphenyl of 7 to 10 carbon atoms substituted with 0 to 3 halogenatoms of atomic number 9 to 35, R is hydrogen, alkyl of 1 to 8 carbonatoms substituted with 0 to 1 halogen atom of atomic number 9 to 35,phenyl or alkylphenyl of 7 to 10 carbon atoms substituted with 0 to 3halogen atoms of atomic number 9 to 35, or phenoxyalkyl, the alkyl grouphaving 1 to 4 carbon atoms, substituted with to 3 halogen atoms ofatomic number 9 to 35 on the benzene nucleus.

2. Compound of claim 1 wherein R is alkyl of 1 to 4 carbon atoms orphenyl substituted with 0 to 3 halogen atoms of atomic number 9 to 35.

3. Compound of claim 1 wherein R is hydrogen, alkyl of 1 to 4 carbonatoms substituted with 0 to 1 halogen atom of atomic atoms substitutedwith 0 to 1 halogen to 3 halogen atoms of atomic number 9 to 35, orphenoxyalkyl, the alkyl group having 1 to 4 carbon atoms, substitutedwith 0 to 3 halogen atoms of atomic number 9 to 35 on the benzenenucleus.

4. Compound of claim 3 wherein R is alkyl of 1 to 4 carbon atoms orphenyl.

5. Compound of claim 1 wherein R is alkyl of 1 to 4 carbon atoms orphenyl, R is hydrogen, methyl, chloromethyl, phenyl or phenoxymethylsubstituted with 1 to 2 chlorine atoms on the benzene nucleus.

6. A method of preparing compound of claim 1 which comprises reacting anN-substituted cyanoformamide or cyanothioformamide of the formula.

with an approximately equal molar quantity of an N-(l,2,2,2-tetrachloroethyl) carboxamide of the formula 2,785,175 3/1957Christian 260309.7

3,140,290 7/1964 LaFon 260309.7

FOREIGN PATENTS 1,036,280 7/1966 Great Britain 260309.7

247,956 12/1969 U.S.S.R. 260309.7

OTHER REFERENCES Edward et al. I Can. J. Chem. Vol. 45, pp. 1925-34(1967). QD1.C2.

Edward et 2.1. II Chem. Abst. vol. 49, column 12303 (1955). QD1.A51.

NATALIE TROUSOF, Primary Examiner U.S. Cl. X.R.

71-92; 260465 D, 465 13, 465.4, 465.5 R, 465.5 A, 558 R, 558 D, 561 R,561 HL; 424--273

